Synthetic resin and method of producing



Patented July W, 1936 SWN'EHETM'} RENEW W ltlilE'lElElUm Willi PRlllllJ'lCllNG lilo Drawing.

Application Uctober it, 1933 Serial No. 6%,063

in Claims.

This invention relates to a new composition of matter and method for its production.

In accordance with this invention a novel synthetic resin, having characteristics renderingfit valuable for use variously in the commercial arts,

is prepared by reacting together dipentene, maleic anhydride and rosin or abietic acid. The reaction involved is probably explained' on the basis of the unsaturated bond of the maleic anhydride 1 reacting with the unsaturated bonds of the dipentene and the abietic acid. The new composition is a highly acidic material of complex nature.

in preparing the synthetic resin in accordance with my invention the reagents may be reacted in widely varying proportions depending upon the physical characteristics desired for the resin product with consideration to the use to which it is to be put. Generally speaking, it is de- W sirable to employ maleic anhydride approximate" ly in the proportion necessary to completely satisfy the reactivity of the dipentene and the abletic acid. 'lhus, ior. example, with use of relatively large amounts or dipentene, the product is soft and tough, with more abietic acid in pro portion to dipentene, the product is hard and brittle, and so on; it being clear that by varying the proportions and amounts oi the reagents products having varying characteristics may be m produced. its illustrative, for example, dlpentene may be used within the range ill to on mole, maleic anhydride within about the range G2 to 2.0 moles and abietic acid within about the range 0.1 to 0.9 mole.

lDipentehe comprises the major portion oi a terpene cut boiling within about the range lib-178 C. obtained by fractionation oi crude turpentine from the Pious palustris, and this terpene out may he used in place oi pure di pentene within the scope of this invention. However, it is preferred to use a pure-dipentene boiling at l'il.5-l'l'?.5 (3., which may be obtained as amiddle out between pin'e oil and turpentine. in preparing the improved synthetic resin the m reagents willbe reacted in the presence of heat.

However, it will he expressly understood that any means for effecting the reaction is contem plated as within the scope of this invention.

Em Any suitable temperature may be used, though a temperature within the range (say) about lee-o C. isdesirable. The reaction will usually be carried out under atmospheric pressure.

but with variations of temperature procedure under reduced or super pressure will obviously be within the scope oi my invention. the pro duction of the resin in accordance with this invention may be carried out in any suitable apparatus, as any suitable container in which the reagents may be heated On completion of the reaction any volatile unreacted matter may be removed or separated from the product by the application of a vacuum to the reaction mass before cooling.

' As a specific illustration, for example, parts by weight of dipentene, parts of abietic acid and 98- parts of maleic anhydride are heated together at a temperature of approximately 200 C. for about 3 hours. The pressure on the reaction mass is then reduced to about 15 mm. of mercury and any unreacted maleic anhydride and the inert ingredients associated with the dipentene are distilled oii".

The reaction product obtained by the above procedure will be found to have a direct acid number of about 230, saponification value of about tit, melting point (drop method) of about 95 C. and a rhodanometric iodine value or 23.1.

As illustrative of various amounts of the several reagents which may be reacted to produce resins in accordance with this invention, for example, the reagents may be reacted in the various proportions given in the following table:

Dipentene Rosin Maleic anhydride Parts by weight Parts by weight Parts by weight 188 20 98 42 98 The several reagents in, for example, the pro portion given in the above table may be reacted in any suitable container, at a temperature (say) within the range l50 C.-7Z5ll C. for (say) one to five hours. Volatile unreacted matter may,

. as has been indicated, be removed on completion till till

a polyhydric alcohol the following is illustrative:

About 100 parts by weight of the above reaction product and 58 parts of glycerol areheated at a temperature of 200 C. for 6 hours'followed by heating at 250 for one hour. The resulting resin has an acid number of 30. and a melting point (drop method) of approximately 113 C. It is highly desirable for use in lacquers and varnishes. Drying or semi-drying oils or their acids may be. added.

Esterification with monohydric alcohols may likewise be carried out, in the case of low boiling alcohols preferably under pressure.

It will be understood that in producing the compositions comprising this invention abietic acid as such may be used or rosin, either wood or gum, preferably high in abietic acid content may be used equivalently.

It is also contemplated to use in place of abietic acid other compounds containing the abietyl radical such as, for example, esters of abietic acid with monohydric or polyhydric alcohol as methyl, ethyl, propyl alcohols, glycol, glycerol, etc. When an ester of abietic acid is employed, the acidity of the reaction product is lower due to the fact that one carboxyl group is esterified. 7

As a specific illustration, for example, of the use of an ester of abietic acid, parts by weight of dipentene, 158 parts of methyl abletate and 98 parts of maleic anhydride are heated together at a temperature of about 200 C. for three hours. The pressure is then reduced to 15 mm. of mercury and the excess of maleic anhydride and the inert ingredients associated with the dipentene are removed.

It will also be understood that maleic acid is contemplated as an operable equivalent of maleic anhydride in the reaction within the scope of this invention.

What I claim and desire to protect by Letters Patent is:

1. A synthetic resin comprising the reaction product of dipentene, maleic anhydride and abietic acid. 1

2. A synthetic resin comprising the reaction product of dipentene, about 15-150 parts by weight, maleic anhydride about 20200 parts by weight and abietic acid about 30-300 parts by weight.

3. A synthetic resin comprising the reaction product of a terpene cut boiling at 170-178" C., maleic anhydride, and a compound containing the abietyl radical.

4. The method of producing a synthetic resin which includes reacting dipentene, maleic anhydride and abietic acid.

5. The method of producing a synthetic resin which includes reacting dipentene, maleic anhydride and abietic acid under the influence of heat.

6. The method of producing a synthetic resin which includes reacting dipentene, maleic anhyaoatgooe dride and abietic acid under the influence of heat at a temperature of about -250 C.

7. The method of producing a synthetic resin which includes reacting dipentene, maleic anhydride and abietic acid under the influence of heat and reducing the pressure on the reaction mass to efiect volatilization of unreacted matter.

8. A synthetic resin comprising the reaction product of dipentene, maleic anhydride and an abietie acid ester.

9. The method of producing a synthetic resin which includes reacting dipentene, maleic anhydride and an abietic acid ester, said ester being of a character such that the abietyl radical is available for reaction.

10. A synthetic resin comprising the reaction product of dipentene, maleic anhydride and a compound containing the abietyl radical.

11. The method of producing a synthetic resin which includes reacting dipentene, maleic anhydride and a, compound containing the abietyl radical, said compound being of a character such that the abietyl radical is available for reaction.

12. The method of producing a synthetic resin which includes reacting under the influence of heat dipentene, maleic anhydride and a compound containing the abietyl radical, said compound being of a character such that the abietyl radical is available for reaction.

13. The method of producing a synthetic resin which includes reacting a terpene cut boiling within the range about C. to about 178 C. and containing dipentene with maleic anhydride and.a compound containing the abietyl radical, said compound being of a character such that the abietyl radical is available for reaction.

14. The method of producing a synthetic resin which includes reacting under the influence of heat dipentene, maleic acid and a compound containing the abietyl radical, said compound being of a character such that the abietyl radical is available for reaction.

15. A synthetic resin comprising the reaction product of a terpene cut boiling within the range about 170 C. to about 178 C., and containing dipentene with maleic anhydride and rosin.

16. The method of producing a synthetic resin which includes reacting under superatmospheric pressure dipentene, maleic anhydride and a compound containing the abietyl radical, said compound being of a character such that the abietyl radical is available for reaction.

17. The method of producing a synthetic resin which includes reacting a terpene cut boiling within the range about 170 C. to about 178 C., and containing dipentene with maleic anhydride and rosin under the influence, of heat at a temperature of about125-250 C.

HAYWARD H. COBURN. 

